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Search results; Over 1,000 homes in Southold

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Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
Studio, 2 beds, 1 private bathroom
20–25 Sept
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4.95 out of 5 average rating, 159 reviews
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Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
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Top guest favourite
Home in East Hampton
Beautiful east hampton cottage by the bay
4 bedrooms, 2 queen beds, 2.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 16 reviews
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Luxe
Home in Montauk
Montauk modern 7-bedroom Heated Pool & hot tub
7 bedrooms, 10 beds, 5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Home in East Hampton
Designer East Hampton with Bay Views + Pool
4 bedrooms, 4 beds, 3.5 bathrooms
25–30 Sept
5.0 out of 5 average rating, 31 reviews
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Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
10–15 Nov
4.99 out of 5 average rating, 105 reviews
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Top guest favourite
Home in East Marion
POOL + Beach Oasis! Winter deals 2+ nights!
5 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
4.97 out of 5 average rating, 30 reviews
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Home in East Hampton
East Hampton Beach House | Private Beach
4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Sag Harbor
9 Acre Luxury Compound in Sag Harbor NY
7 bedrooms, 10 beds, 8.5 bathrooms
11–16 Oct
4.99 out of 5 average rating, 148 reviews
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Top guest favourite
Cottage in Sag Harbor
Hamptons Waterfront Getaway – Stylish & Serene
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Orient
Luxury Escape - Saltwater Pool
4 bedrooms, 7 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Holiday home in Orient
Private Vineyard w/Pool, Walk to Beach & Village
3 bedrooms, 4 beds, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Sag Harbor
Brick Kiln
4 bedrooms, 4 beds, 3.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.97 out of 5 average rating, 131 reviews
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Top guest favourite
Home in Clinton
Luxury 5 BR Beachfront Retreat
5 bedrooms, 8 beds, 3 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 9 reviews
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Top guest favourite
Home in East Marion
Long Island home with pool 1 mile from Greenport
3 bedrooms, 3 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 24 reviews
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Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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Guest favourite
Home in Orient
Orient Point Family Waterfront Home
5 bedrooms, 9 beds, 3.5 bathrooms
3–8 Oct
4.96 out of 5 average rating, 27 reviews
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Home in East Hampton
Remarkable East Hampton Getaway with Pool
3 bedrooms, 3 beds, 3 bathrooms
23–28 Sept